500169-90-4

Basic information

• Product Name: 2-(4-CHLORO-PHENYL)-6-ETHYLSULFANYLTHIOPYRAN-4-ONE
• Synonyms: 2-(4-CHLORO-PHENYL)-6-ETHYLSULFANYLTHIOPYRAN-4-ONE
• CAS NO: 500169-90-4
• Molecular Formula: C₁₃H₁₁ClOS₂
• Molecular Weight: 282.81
• Product Categories: pharmacetical
• Mol File: 500169-90-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 424.285°C at 760 mmHg
• Flash Point: 210.4°C
• Appearance: /
• Density: 1.354g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.664
• CAS DataBase Reference: 2-(4-CHLORO-PHENYL)-6-ETHYLSULFANYLTHIOPYRAN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-CHLORO-PHENYL)-6-ETHYLSULFANYLTHIOPYRAN-4-ONE(500169-90-4)
• EPA Substance Registry System: 2-(4-CHLORO-PHENYL)-6-ETHYLSULFANYLTHIOPYRAN-4-ONE(500169-90-4)

Safety Data

• Hazardous Substances Data: 500169-90-4(Hazardous Substances Data)

Usage

Type of compound

Thiotetronic acid derivative

Known for

Potent analgesic effects

Comparison

Similar to fentanyl

Usage

Recreational purposes (due to strong opioid activity)

Status

Controlled substance in many countries

Medical approval

Not approved for medical use

Potential risks

Dangerous and potentially lethal when not used under strict medical supervision

Potency

High potency substance

InChI:InChI=1/C13H11ClOS2/c1-2-16-13-8-11(15)7-12(17-13)9-3-5-10(14)6-4-9/h3-8H,2H2,1H3

Upstream product

• 150444-52-3 (Z)-1-(4-Chloro-phenyl)-3-hydroxy-but-2-en-1-one 
• 99-91-2 para-chloroacetophenone 
• 6302-55-2 1-(4'-chlorophenyl)-1,3-butanedione 
• 620158-95-4 2-(4-chlorophenyl)-6-ethylthio-2,3-dihydrothiopyran-4-one 
• 75-03-6 ethyl iodide 
• 500169-97-1 6-(4-chlorophenyl)-2-mercapto-4H-thiopyran-4-one 

Downstream Products

• 500169-20-0 2-(4-chlorophenyl)-6-morpholino-4H-thiopyran-4-one 

Relevant articles and documents

Pyranone, thiopyranone, and pyridone inhibitors of phosphatidylinositol 3-kinase related kinases. Structure-activity relationships for DNA-dependent protein kinase inhibition, and identification of the first potent and selective inhibitor of the ataxia telangiectasia mutated kinase

Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholinopyran-4-ones and 2-morpholino- thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6- (morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.

2,6-Disubstituted pyran-4-one and thiopyran-4-one inhibitors of DNA-dependent protein kinase (DNA-PK)

6-Aryl-2-morpholin-4-yl-4H-pyran-4-ones and 6-aryl-2-morpholin-4-yl-4H-thiopyran-4-ones were synthesised and evaluated as potential inhibitors of the DNA repair enzyme DNA-dependent protein kinase (DNA-PK). Several compounds in each series exhibited super